Dimethylformamide → HCID 11132852, compound

HRID 2300694Notes

Reaction equation

HRID 2300694 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[CH3:23][C:24]1[NH:25][CH:26]=[CH:27][N:28]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:25]3[CH:26]=[CH:27][N:28]=[C:24]3[CH3:23])[O:3][C:4]=2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 11099941HCID 11099941, compound

Product 1

HCID 11132852HCID 11132852, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of ethyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepentanoate(10.0 g), 2-methylimidazole(7.20 g), potassium carbonate(12.1 g) and N,N-dimethylformamide(80 ml) was stirred for 2 hours at 120-130° C. Water was added to the reaction mixture to give ethyl 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepentanoate(9.97 g, 88%). This was recrystallized from ethyl acetate-isopropyl ether to give colorless prisms. mp 93-94° C.

Sources & evidence

ORD record
ord-c3d9066082a24204b362b85d05ba638a
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

Loading…